The uncertainty within the agricultural supply chain often leads to substantial wastage and unmet demand, underscoring the imperative of addressing the crop planning problem within agricultural supply chain management. In this paper, we developed a set of mathematical programming models that considers both the free market scenario and the contract farming scenario. The model accounts for yield and price volatility induced by meteorological and market conditions. Through the simulation of real-world crop planning scenarios using mathematical models, the planning problems faced by both farmers and consumers in building optimal matching mechanisms to obtain optimal overall farm revenue are evaluated. Numerical experiments have been conducted to validate the model, and we present management recommendations tailored to various scenarios.